六水硝酸铽 → 2,3,8,9-Tetramethoxybenzo[i]phenanthridine

HRID 369758笔记

反应方程式

HRID 369758 反应方程式
[CH3:1][O:2][C:3]1[CH:4]=[C:5](Br)[C:6]([N+:11]([O-])=O)=[CH:7][C:8]=1[O:9][CH3:10].[CH3:15][O:16][C:17]1[CH:18]=[C:19](Br)[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].[N+]([O-])(O)=O>C(O)(=O)C>[CH3:15][O:16][C:17]1[C:22]([O:23][CH3:24])=[CH:21][C:20]2[C:8]3[CH:7]=[N:11][C:6]4[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=4[C:3]=3[CH:4]=[CH:5][C:19]=2[CH:18]=1

参与物

5

反应物 3

HCID 944六水硝酸铽HCID 761144-溴黎芦醚HCID 1709684-溴-5-硝基邻苯二甲醚2 次

产物 1

HCID 98847232,3,8,9-Tetramethoxybenzo[i]phenanthridine收率 92%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂

反应条件

温度
10 °C

实验过程

3,4-Dimethoxy-6-nitro-bromobenzene (16). 3,4-Dimethoxybromobenzene (5 g, 23 mmol) was slowly added to a stirred solution of 35 mL concentrated nitric acid and 105 mL glacial acetic acid maintained at 10° C. The reaction mixture was stirred at 15° C. for 1 h and then diluted with 200 mL ice cold water. The resulting mixture was extracted thrice with 200 mL portions of ether. The combined organic phase was dried and evaporated in vacuo. The crude product was recrystallized from ethanol to give bright yellow needle shaped crystals of compound 16 in 92% yield; mp=122-124° C.; IR (Nujol) 1510, 1312; 1H NMR δ 3.94 (3H, s), 3.97 (3H, s), 7.12 (1H, s), 7.57 (1H, s); 13C NMR δ 56.9, 57.2, 108.0, 109.5, 117.0, 148.7, 153.3; Anal. calcd for C8H8NO4Br: C, 36.72, H, 3.14, N, 5.30; Found: C, 36.70, H, 3.13, N, 5.29.

后处理

  1. extractionThe resulting mixture was extracted thrice with 200 mL portions of ether
  2. customThe combined organic phase was dried
  3. customevaporated in vacuo
  4. customThe crude product was recrystallized from ethanol
  5. customto give bright yellow needle

来源与证据

ORD记录
ord-c1ca8439c99c47b08db926ebbb9216b9
来源数据集
uspto-grants-2000_10
专利号
US06140328

反应笔记

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